文献类型：期刊文献

英文题名：Efficient and Practical Syntheses of Enantiomerically Pure (S)-(-)-Norcryptostyline I, (S)-(-)-Norcryptostyline II, (R)-(+)-Salsolidine and (S)-(-)-Norlaudanosine via a Resolution-Racemization Method

作者：Zhu, Ruiheng[1];Xu, Zhangli[1];Ding, Wei[1];Liu, Shiling[1];Shi, Xiaoxin[1];Lu, Xia[1]

机构：[1]E China Univ Sci & Technol, Sch Pharm, Dept Pharmaceut Engn, Shanghai 200237, Peoples R China

年份：2014

卷号：32

期号：10

起止页码：1039

外文期刊名：CHINESE JOURNAL OF CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000343871100018)】；

基金：We thank the National Natural Science Foundation of China (No. 20972048) for the financial support of this work.

语种：英文

外文关键词：tetrahydroisoquinolines; norcryptostyline; salsolidine; norlaudanosine; resolution; racemization

摘要：Four racemic tetrahydroisoquinolines (RS)-(+/-)-1-4 were prepared from homoveratrylamine via amidation, Bischler-Napieralski reaction and the subsequent reduction. The enantiomerically pure tetrahydroisoquinolines (S)- (-)-norcryptostyline I [(S)-(-)-1], (S)-(-)-norcryptostyline II [(S)-(-)-2], (R)-(+)-salsolidine [(R)-(+)-3] and (S)-(-)-norlaudanosine [(S)-(-)-4] were then obtained in 45%, 40%, 41% and 38% yields, respectively, via resolution of the racemic compounds (RS)-(+/-)-1-4 with half equivalent of chiral acids. In addition, the enantiomerically enriched compounds (R)-(+)-1, (R)-(+)-2, (S)-(-)-3 and (R)-(+)-4 from the mother liquors were efficiently racemized via a one-pot redox method in almost quantitative yields.